I've got 21,074 Cubs cards from 316 different brands listed on a spreadsheet. A random number generator picked five cards, one each from the past several decades.
1980s: 1987 Team Issued Keith Moreland The Cubs gave away these cards on July 29, 1987. Moreland was 1-3 that day (a triple!) but the Expos trounced the Cubs 11-3.
1990s: 1993 O-Pee-Chee #8 Steve Buchele This card is from OPC's first original set. The design is pretty underwhelming.2000s: 2003 Leaf #140 Corey Patterson Patterson was putting up decent number (.298, 13 HR, 55 RBIs, 16 SBs), but his 2003 season ended abruptly when he tore his ACL on July 6.